
Apartment holiday rentals in Wintergreen Resort
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Top-rated apartment rentals in Wintergreen Resort
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Panoramic Sunsets, Mountain Views, Private Deck.
Wake up above the mountains and end your day with unforgettable sunset views some of the best on the mountain. Sunset Vista Villa is a cozy retreat designed for slowing down, morning coffee on the deck, evenings by the fire. With two private bedrooms, each with its own en-suite bathroom, its perfect for couples or friends. Easy entry with just a few steps, yet elevated views make this stay both convenient and special. Ask us about early check-in or late check-out to enjoy even more of the view

Where the Trail Ends
Some trips are about doing everything. This one’s about slowing down. Nestled inside Wintergreen Resort, this updated mountain retreat puts hiking trails, ski slopes, wineries, and breweries at your door - then gives you a warm space to come home to. Curl up by the fireplace, cook a real meal in a full kitchen, or take the morning slow on your private patio with mountain views. When you’re ready to explore, everything is close. When you’re not, the community pool and quiet will keep you busy.

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Luxury Condo in the Sky! Finest in Wintergreen!
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

2-min drive to resort, Outdoor HOA pool opens 5/25
Peaceful, recently renovated mountain-top retreat. Relax or work from home. End your day with a hike or spa treatment around the corner—linger with a glass of wine at sunset. It’s all only a 2 minute walk from the front door. Welcome to our mountain home! 2-3 min drive from ski lifts/resort, hiking Free firewood (seasonal) Family games & smart TVs (no cable) for movie night (must sign into your own subscriptions) Smartlock entry Stair-free entry *outdoor HOA pools CLOSED for season

Eight Minute Walk to Everything
This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

3 BR 3 BA, 2 story condo in Highlands
Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

1 bedroom condo, close to hikes & breweries & pool
Cozy 1BR Wintergreen condo 🌳 🌄 Close to scenic hikes, local breweries and wineries. The resort village, and mountain-top market, just minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax after a day outdoors and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and or cool off in the heated community pool.

BlueRidge Getaway- Dog Friendly
Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Cozy Comfort with a View - Wintergreen Resort
Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.

Ski-In Ski-Out ~ Mtn Views ~ King Suite
Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

Your Cozy Mountain Getaway Awaits
This beautifully renovated 2 BR/2 BA mountain condo is centrally located in the Wintergreen Resort - walking distance to the Wintergreen ski resort, tubing park, restaurants and the market! Park your car with no need to move it during your visit. The condo comes fully stocked (including firewood) and is the perfect place for your getaway, including your furry friends (fee).
Popular amenities for Wintergreen Resort apartment rentals
Weekly apartment rentals

Hike, Swim, Golf, Spa & More! Wintergreen Resort

Ty's Retreat: Cozy 2-bedroom condo with fireplace

2 br/2 b condo; skiing; hiking; wineries; pool

Wintergreen Ski Retreat, Cozy Condo Near Slopes

Ski-in/Ski-out condo Pet-OK Steps from Wintergreen

Live the Dream at Wintergreen: Pet-friendly, Pool

Cozy remodeled studio overlooking 18th hole

Lovely Ski Front Private 3-bed/3-bath condo
Pet-friendly apartment rentals

All-Season 2bd/2ba next to Spa view of Golf Course

Wintergreen! Dog friendly, cozy and comfortable

Condo with Valley Views!

Buena Vista Panoramic Retreat: Million Dollar View

1720 High Ridge at Wintergreen Resort

New Construction! 1 Bed/2 Bath, pet friendly

Beautiful Mountain Getaway - Walk to Everything!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Apartment rentals with a pool

Pepper's Mountain Pad

Uncork and unwind Mountain Retreat

Cozy condo! Short walk to the slopes and trails.

On the mountain, pet and child friendly

Relaxation in the Mountains

Amazing views! Overlooking Expert Slope

A Mountain Escape-Cozy Condo for 2 to 4

Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £137 | £131 | £111 | £97 | £94 | £94 | £103 | £98 | £97 | £110 | £105 | £123 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about apartment rentals in Wintergreen Resort

Total holiday rentals
Explore 330 holiday rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort holiday rentals start at £53 per night before taxes and fees

Verified guest reviews
Over 10,180 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
280 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
330 of Wintergreen Resort holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wintergreen Resort rentals

4.8 Average rating
Wintergreen Resort stays are highly rated by guests – averaging 4.8 out of 5!
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- Shenandoah National Park
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- Wintergreen Resort
- Devils Backbone Brewing Co Basecamp
- Blenheim Vineyards
- James Monroe's Highland
- Virginia Horse Center
- Cardinal Point Winery
- Monticello
- Amazement Square
- Frontier Culture Museum
- Glass House Winery
- Liberty Mountain Snowflex Centre
- John Paul Jones Arena
- James Madison University
- The Rotunda
- Natural Bridge State Park
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Grand Caverns
- IX Art Park
- James Madison's Montpelier
- White Lotus Eco Spa Retreat





